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The Best Chelsea Boots for Men

From best-value to best-in-class, our guide to Chelsea boots covers ready-made designs from new brands and bespoke pairs from legacy makers.


Chelsea boots originated in England in the mid-19th century. Then, they were called "Paddock boots," a short men's boot style for equestrian functions. They've only strayed from home — and horse riding — just recently. The elasticized wonders were a staple in mid-’60s London scenes and protected the feet of seemingly every British invader — from John Lennon to Ringo Starr. Recently, they’ve seen a revival on many of menswear’s best-dressed.

What Are Chelsea Boots?

Marked by a slim silhouette, elastic side panels, and heel pull tabs, the Chelsea boot has seen reinterpretations in leather, suede, and neoprene, either with crepe, leather or rubber soles. They're a versatile option that's gone largely unchanged since inception, save for material swaps here and there. And while they aren't as in demand as they were in the mid-2010s — when everyone from Kanye West and David Beckham to Harry Styles and Justin Theroux was wearing theirs — the best Chelsea boots for men prove sensible now more than ever. The style emphasizes both aesthetics and comfortability, meeting in a middle ground where both camps — those wearing them for their look and those wearing them for their convenience — are appeased.

How to Wear Chelsea Boots

Designers from all over have riffed on the shape over and over and over again, resulting in a rich landscape of iterations to choose from. Whether you're looking for a pair that's polished or preppy (to wear with an Oxford and chinos), with a bit of street cred (to wear with jeans and a hoodie) or suit-friendly (to wear with a, well, suit), there is a Chelsea boot for everyone.

There are a number of ways to wear Chelsea boots — a statement that seems relatively straightforward. But with Chelsea boots, or at least certain styles of Chelsea boots, which ebb and flow in and out of fashion's good graces, it can be hard to stay current. Leather is generally a better choice than suede, I’d say, both because of traditional leather’s durability but also its longevity. Hide will look better than center-cut suede five years from now if your Chelsea boots make it that long. But any good one should.

How to Choose the Right Chelsea Boot for You

Options abound — from suede styles to patent leather pairs. There are knit options as well. Or even rubberized iterations. Which you buy depends on where you wear them, and what for.

"Right now, I'm loving the chunky Chelsea boot style for men," celebrity stylist Vanessa Powell says. "Chelsea boots are a closet staple, but the added lug makes this classic more hip to the streetwear trends. Plus, [most] are all-weather friendly so you can tackle the elements in style."

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Best Overall Chelsea Boots
Blundstone BL558 Boots
Best Upgrade Chelsea Boots
R.M. Williams Craftsman Boot
Best Affordable Chelsea Boots
Rhodes Blake Boot
Best Suede Chelsea Boots
Common Projects Suede Chelsea Boots
Best Goodyear Welt Chelsea Boots
Oak Street Bootmakers 5504 Chelsea Boot
Best Lug Sole Chelsea Boots
Blundstone Lug Boot
Best Outdoor Chelsea Boots
Diemme Balbi Suede Ankle Boots
Best Weatherproof Chelsea Boots
Nisolo All-Weather Chelsea Boot
Best Rubber Chelsea Boots
Hunter Original Chelsea
Best Machine Washable Chelsea Boots
Rothy's The Chelsea Boot
Best Black Leather Chelsea Boots
Unmarked Chelsea Toro Special Edition
Belstaff Longton Leather Chelsea Boot
Oliver Cabell Chelsea Boot
New Republic Sonoma Suede Chelsea Boot
Now 23% off
Grant Stone Chelsea Boot
Astorflex Bitflex
Adelante Mendoza Chelsea Boot
Dr. Martens 2976 Bex Smooth Leather Chelsea Boots
Beckett Simonon Bolton Chelsea Boots
Tecovas The Chance
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